5,11,17,23-tetra-tert-butyl-25,27-dihydroxy-26-(benzyloxy)-28-(2-pyridylmethoxy)calix<4>arene | 150112-04-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,11,17,23-tetra-tert-butyl-25,27-dihydroxy-26-(benzyloxy)-28-(2-pyridylmethoxy)calix<4>arene
• 英文别名: 5,11,17,23-tetra-tert-butyl-25,27-dihydroxy-26-(benzyloxy)-28-(2-pyridylmethoxy)calix[4]arene；5,11,17,23-tetratert-butyl-26-phenylmethoxy-28-(pyridin-2-ylmethoxy)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,27-diol
• CAS: 150112-04-2
• 化学式: C₅₇H₆₇NO₄
• 分子量: 830.163
• InChiKey: IRJDNOIMTAMIQB-UHFFFAOYSA-N

物化性质

• 沸点：
  841.9±65.0 °C(Predicted)
• 密度：
  1.094±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.52
• 重原子数：
  62.0
• 可旋转键数：
  6.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  71.81
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  溴丙烷 、 5,11,17,23-tetra-tert-butyl-25,27-dihydroxy-26-(benzyloxy)-28-(2-pyridylmethoxy)calix<4>arene 在 barium dihydroxide 、 barium(II) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以76%的产率得到5,11,17,23-tetra-tert-butyl-25-hydroxy-26-(benzyloxy)-27-propoxy-28-(2-pyridylmethoxy)calix<4>arene
  参考文献：
  名称：

  Syntheses and optical resolution of calix[4]arenes with molecular asymmetry. Systematic classification of all possible chiral isomers derivable from calix[4]arene

  摘要：

  All possible chiral isomers that can be derived from calix[4]arene by modification of the OH groups were systematically classified. Molecular asymmetry can be generated not only by different substituents but also by conformational isomerism. The numbers of chiral isomers are 24 for tetra-O-substituted calix[4]arenes, 10 for tri-O-substituted calix[4]arenes, 3 for di-O-substituted calix[4]arenes, and 0 for mono-O-substituted calix[4]arenes. This implies that calix[4]arene is a useful building block for the design of novel asymmetric ring structures. In order to demonstrate asymmetry in these chiral calix[4]arenes, we synthesized several tetra-, tri-, and di-O-substituted calix[4]arenes by using the metal template method, the stepwise synthesis method, the protection-deprotection method, etc., which were developed in efforts directed toward regioselective O-alkylation and control of conformational isomerism in calix[4]arenes. Finally, we succeeded in complete optical resolution of chiral calix[4]arenes by an HPLC method using a chiral-packed column or by the formation of diastereomers with the (-)-menthoxyacetyl group. This article thus contains all of the molecular design concepts, syntheses, and optical resolutions of chiral calix[4]arenes.

  DOI：

  10.1021/ja00063a020
• 作为产物：
  描述：

  5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene 在 barium dihydroxide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 54.0h， 生成 5,11,17,23-tetra-tert-butyl-25,27-dihydroxy-26-(benzyloxy)-28-(2-pyridylmethoxy)calix<4>arene
  参考文献：
  名称：

  Syntheses and optical resolution of calix[4]arenes with molecular asymmetry. Systematic classification of all possible chiral isomers derivable from calix[4]arene

  摘要：

  All possible chiral isomers that can be derived from calix[4]arene by modification of the OH groups were systematically classified. Molecular asymmetry can be generated not only by different substituents but also by conformational isomerism. The numbers of chiral isomers are 24 for tetra-O-substituted calix[4]arenes, 10 for tri-O-substituted calix[4]arenes, 3 for di-O-substituted calix[4]arenes, and 0 for mono-O-substituted calix[4]arenes. This implies that calix[4]arene is a useful building block for the design of novel asymmetric ring structures. In order to demonstrate asymmetry in these chiral calix[4]arenes, we synthesized several tetra-, tri-, and di-O-substituted calix[4]arenes by using the metal template method, the stepwise synthesis method, the protection-deprotection method, etc., which were developed in efforts directed toward regioselective O-alkylation and control of conformational isomerism in calix[4]arenes. Finally, we succeeded in complete optical resolution of chiral calix[4]arenes by an HPLC method using a chiral-packed column or by the formation of diastereomers with the (-)-menthoxyacetyl group. This article thus contains all of the molecular design concepts, syntheses, and optical resolutions of chiral calix[4]arenes.

  DOI：

  10.1021/ja00063a020

文献信息

• Iwamoto Koji, Shimizu Hiroyasu, Araki Koji, Shinkai Seiji, J. Amer. Chem. Soc., 115 (1993) N 10, S 3997-4006
  作者：Iwamoto Koji, Shimizu Hiroyasu, Araki Koji, Shinkai Seiji

  DOI：——

  日期：——